Durand's website describes Mr McShane as its premises manager, though he was also named by the trust as its caretaker when contacted by Tes.

A source in the academy trust's governing body said: "The governors were completely unaware that this payment had been made. The first we heard of it was when the auditors alerted us."

Mr McShane was paid between £100,000 and £105,000 in 2016-17, according to the trust's latest financial accounts – an increase from the £75,000 to £80,000 he received the previous year.

Tes data shows that premises managers attract an average salary of between £27,500 to £31,500 in London, and £21,550 to £24,00 outside of London.

Phillip Reynolds, senior manager at accountancy firm Kreston Reeves who works with the academies sector, said: "Anything above £40,000 is odd, unless it's for a large multi-academy trust."

Asked how common it was for academies to pay a lump sum in lieu of years of accrued annual leave, he said: "I've definitely not seen that before."

In the commercial sector, it was not unheard of for a payment to be given to an employee who had agreed not to take annual leave while working hard on a particular project, he said. "But even then, eight years seems outside the norm."

He added: "And this isn't commercial, this is a school. It's public money."

Mr McShane is a trustee of Durand Academy Trust (DAT) as well as being a director of Durand Education Trust (DET) – the company that owns the land on which the school sits and at which Mr McLaughlin is also a director.

The Education and Skills Funding Agency has previously demanded that no DAT director was also a director of DET.

DET contracts London Horizons, the firm owned by the school's outspoken founder Sir Greg Martin, to run a leisure facility on the school site.

A Durand Academy Trust spokesman said: "The payment was made for the holidays which Mr McShane was entitled to as per his employment contract with the academy, and the holidays had been accrued over the last eight years because of ongoing major building works at different sites.

"It is understood that there had been arrangements between the staff member and the senior management of the academy that any accrued holidays would be utilised at a future period.

"This arrangement was appeared to have been historically approved by the board. In April 2017, the staff member was offered payment in lieu of the accrued holidays."

Regarding Mr McShane's directorship of DET, the spokesperson said Durand was "seeking further advice on this matter".

A DfE spokesperson said: “It is essential that taxpayers’ money is used responsibly. We investigate all allegations of financial impropriety. Following previous findings of financial mismanagement, Durand Academy Trust’s funding agreement will be terminated on 29 June 2018.

“As outlined in the notices sent in July 2016 and October 2016 there have been serious concerns about the financial management and governance of the trust. We continue to have those concerns and have accordingly taken this termination action.”

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